


Kinktober 2019

by Minagi_Writes_Shit



Category: Undertale (Video Game)
Genre: Awkwardness, Dry Humping, F/M, I swear there will be sex eventually, Multi, Sans is smol, Sexy Times, Smooching, Underswap Sans (Undertale), mostly - Freeform, not gonna use au nicknames unless required by plot, will add tags as chapters come out
Language: English
Status: In-Progress
Published: 2019-10-02
Updated: 2019-10-05
Packaged: 2020-11-15 01:07:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,791
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20857697
Author URL: https://archiveofourown.org/users/Minagi_Writes_Shit/pseuds/Minagi_Writes_Shit
Summary: Y'all know what this is.





	1. Just Some Info

**Notes for the Chapter:**

> You know what this is.

It’s that time of year, so here comes an influx of (hopefully) steamy oneshots! They are all going to be stupidly self indulgent, cuz that’s just how I write. This will also be completely Sans-centric, though I haven’t decided who all I plan on using. For any of you who are curious about prompts, I have taken fondly to a list provided here! 

https://twitter.com/DevilChicky210/status/1176209944456126466?s=19

Give them a nudge if you like their list, because I certainly do~! Now, onto the nitty gritty details. As you can see, some of these prompts (somno for example) definitely fall into the dubcon category. I’m doing this for fun sexy times, and will be keeping dark themes to a _minimum_. 

That being said, if something isn’t your jam, or you don’t feel like the oneshot is moving in a direction you’re comfortable with, _STOP READING_. These are all oneshots, and there’s no crime or penalty for skipping a chapter.

In case the link breaks, or you can’t open it for whatever reason, I will list what’s coming (pun intended) below~

Day 1: Kissing  
Day 2: Grinding  
Day 3: Biting  
Day 4: Spanking  
Day 5: Bondage  
Day 6: Hair Pulling  
Day 7: Aphrodesiac  
Day 8: Toys  
Day 9: Somnophilia  
Day 10: Role play/Costume  
Day 11: Overstimulation  
Day 12: Gang Bang  
Day 13: Tentacles  
Day 14: Exhibitionism  
Day 15: Oral  
Day 16: Cock Worship  
Day 17: Wax Play  
Day 18: Dom/Sub  
Day 19: Romantic  
Day 20: Latex/Leather  
Day 21: Size Difference  
Day 22: Breeding  
Day 23: Pet Play  
Day 24: Face Sitting  
Day 25: Boob Job  
Day 26: Spit Roasting  
Day 27: Double Penetration  
Day 28: Fingering  
Day 29: Dirty Talk  
Day 30: Body Worship  
Day 31: Aftercare

Addendum: My schedule is hella crazy, so I might not be able to get these posted on time every day. But I’ve got something planned for each one, so they’ll definitely be coming!


	2. Day 1: Kissing

**Notes for the Chapter:**

> God, I have no idea what I'm doing. 
> 
> This chapter is classic sans x reader. 
> 
> No dirty deeds in this one, just my poor attempt at smooches.

Ah Grillbys. Your home away from home. Where the atmosphere was warm, and the company lively. You’d been coming here every Friday for going on a year now, and the regular patrons were practically family by this point. There was never a dull moment, and you loved the shenanigans that went on.

Mostly…

“So, would you smooch a skeleton?”

Bugsy, a small rabbit who practically lived at the bar, leaned against you. It was a loaded question that you should have known was coming sooner or later. Happy Hour at grillbys usually turned into Share Embarrassing Facts hour with this group. Everyone was so open to each other, so jovial and ready to share a good laugh at the silly shit life had to offer.

You currently sat with Bugsy, Doggo, a pooch with poor eyesight and a keen sense of smell, and Bill, a birdlike monster who usually spent their time translating for Grillby. Sans, whom you _knew_ Bugsy was hinting at, was at the bar picking up another round of drinks for the table.

“Which skeleton are we talking about?” you asked, the alcohol in your system keeping you lax and smiling despite the butterflies in your stomach.

“Ha! That’s a yes” Bill squaked, translating your returned question without missing a beat.

Of course you’d smooch a skeleton. Your face burned, not ready at all in your drunken state to be having this conversation. You quickly retorted, “I didn’t say that!”

Doggo huffed, a doglike chuckle coming from his muzzle as he interjected. “If the answer was no, it wouldn’t matter _which skeleton_ would it?”

And he was right, but you had a habit of speaking before thinking when drinking.

“Pssshhh, cmon. That’s not...I don’t even…”

You were struggling to find the words to fight back as another round of drinks were set on the table. Sans’ timing couldn’t have been worse, showing up just in time for your flustered self to trip over your own words. His expression was soft, full of mirth as he took in the state of the table.

**“oh, sweet, is it embarrassing facts hour already? spill the beans, what’d i miss?”**

He slipped into the booth next to you, not missing a beat as his proximity forced you to squish closer to Bugsy. Hindsight being 20/20, the lot of you should have probably used a table with chairs since the booths weren’t intended for more than 4 people. But hindsight is a bitch, and you were struggling to hold onto what little composure you might have left as you were sandwiched between the 2 biggest gossips in the room.

Bugsy leaned forward, looking across your compacted body to fill said skeleton in on all the juicy details.

“We were askin’ if she’d smooch a skeleton.”

“Still haven’t heard a no, either~” 

**“really? which skeleton are you thinkin of smoochin?”** His grin was wide as his eyes fixated on you. He was too close, really. The lazy fucker was leaned against you, and you couldn’t tell if it was intentional or due to the lack of space in the seat. 

You really couldn’t meet his gaze as he asked you. You needed to tread lightly, and were pretty sure you were screwed no matter what your answer was. You only knew two skeletons. As far as you were aware, there only _were_ two skeletons. If you told him you wanted to smooch him, you’d never live it down. If you let him think it was Papyrus, you’d never live it down. You were so boned.

“I don’t...I mean...how would that even work?”

Why did you just ask that?!? Fucking drunk brain, that was just going to add fuel to the fire.

**“with your lips, i’d imagine”**, he really never misses a beat with his responses. It’s almost as if monsters were gifted with immediate reactions.

“You do a lot of imagining, sansy?”  
“You don’t have lips”

Bill mocked the skeleton next to you, at the same time you blurted out your own response. Sans eyes lidded as he kept his focus on you, but the slight blue shimmer scattering across his face told the table that he heard Bill in the background.

**“what do i need lips for? the topic of conversation is smoochin’ a skeleton, not being smooched by one.”**

Your imagination tried to run wild as he said that, visages of him leaning in to kiss you shoving its way to the forefront of your mind. You were stuck, unable to even think of a response as you gawked at him. You were pretty sure you were completely found out now. There was no chance of hiding your interest in this goofy idiot.

“How...how does a skeleton smooch, exactly?” You don’t know if it was because of the alcohol, or because your brain stalled as it tried to produce the imaginary scenario, but you know you did NOT mean to say that out loud.

**“what makes you think i can?”**

“Aww, sansy no!”

“You’re so full of shit, dude.”

You found yourself smiling along with everyone at the table. Of course he would deflect the question like that, and you were thankful he did. It was just like him, one of the ridiculous little things you liked about him. This silly banter was your favorite part of coming here, and whatever awkward anxiety you had melted away.

Then Bugsy just had to open her mouth.

“You have to show her!”

Why did she have to say that? He didn’t have to show you, and despite everyone calling you out already, you were NOT about to admit that you wanted him to know. But you saw that blush creep back onto his boney cheeks, and all logic flew out the window.

“Yeah, Sansy, you have to show me!”

Way to dig yourself deeper into this hole of embarrassment. It wasn’t really out of character for you, you had a bad habit of egging Bugsy on when she was on a mission to tease someone. But then Doggo and Bill joined in, teasing the poor skeleton about how he _”had to”_ give you a demonstration.

Sans was practically a blueberry now, glancing around the table and chuckling nervously as the jeering continued from the other monsters. His eyes locked on to yours and he went stiff, frozen for a moment before seeming to make up his mind. His boney eyelids drooped, his expression softening as he reached up to touch your cheek.

**“alright, you asked for it.”**

Your breath caught in your throat as your brain scrambled to register what he’d just said. You stared at him as he leaned closer, sitting up right so he could properly reach your face. Your pulse quickened as you realized he was actually gonna do it, he was gonna frikin kiss you right here in front of everyone at Grillbys. You shut your eyes, the butterflies in your stomach going crazy as the anticipation drove you crazy.

**“mwwwwah!”**

The sound he made was horribly exaggerated as his boney mouth pressed against your cheek. It was like the action someone would make towards a kid, loud and obnoxious and so blatantly fake. You felt his grin widen against your skin, your face a cherry red as your drunken brain once again had to struggle to catch up to the situation.

“Pffffttttahahahaha” 

You broke down laughing, and the rest of the table joined in. This was so ridiculous, so like him. He was such a dork, you couldn’t even pretend to be upset with how he pulled off that little prank. The topic moved on after that, settling down and shifting towards less teasing conversations.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Your group chatted and joked well into the night, before closing your tabs and saying your goodbyes. Nights like these, where you found yourself unable to walk straight and bumping into furniture, sans always offered to take you home. Tonight was no exception, and you accepted his shortcut eagerly.

But tonight, you found yourself fixated on the way his phalanges intertwined with your fingers, leaned just a bit closer as he pulled you into a pseudo, one armed hug. The fur on his jacket ticked your chin slightly, and you lingered for a moment longer than normal after your feet found themselves firmly planted on your living room carpet.

**“doin alright, bud?”**

His voice was softer than usual, quiet. As if he were trying to lure a stray cat out of hiding. Or maybe he was just being considerate of your ear drums. You weren’t sure at this point, too wasted to really mind one way or another. You pulled away from the safety of his embrace, looking down at him as you straightend up. Realizing you hadn’t responded yet, you smiled and said,

“How does a skeleton really kiss?”

…..god. Dammit. That wasn’t what you were gonna say. That convo was done and over with. Everything had smoothed itself out and moved on. You weren’t even consciously _thinking_ about it anymore. So why were those the words that just came out of your mouth?!?

And now everything felt awkward. The silence, the way you stared at each other, mirrored expressions of wide eyes and half-fallen smiles. This was where he turned you down, this was where you fucked up your friendship. Panic began to set in, and you were struggling to find a way to take it back.

**“ya really wanna know?”**

_No. I swear, it’s all good._

“Yes.”

Foot, meet mouth. Your words and your brain were on completely different wavelengths, and you seemed determined to dig your own grave. You found yourself staring at your feet, unable to handle the intensity of his gaze. You could feel your face burning, found yourself wanting to apologize profusely for the situation you just put him in. You wanted to tell him he didn’t have to, that it wasn’t important, that you were just drunk. Any excuse you could find to bury this conversation and pretend it didn’t happen.

**“alright”**

_what?_ You looked back up at him as he shuffled awkwardly. Sans looked nervous, blue dusting his skull as he too seemed focused on his feet. He glanced up at you, attempting a reassuring smile that looked beyond awkward in this situation. Your heart skipped a beat at the sight, your idiotic dork of a friend bashfully engaging this train wreck of a conversation.

**“just don’t blame me if you regret it in the morning”**

He reached out, cupping your cheek as he mirrored his behavior from earlier in the evening. His face was flushed, eyes lidded, as he leaned closer. But you weren’t sitting at the same level this time, and you found yourself being pulled down slightly as he stood on his tiptoes. 

Somehow, you processed the fact that he was going to kiss you again. But he wasn’t aiming for your cheek this time. His teeth parted, revealing just how sharp his teeth actually were, canines far more prominent than they appeared regularly. You could smell the whiskey on his breath, feel the warmth of expelled magic as he got closer.

His eyes closed as your faces almost touched, and you faintly caught a glimpse of blue in his mouth as you mirrored the action. Anticipation was high in the air, and you almost expected him to deliver some sort of punchline instead of a kiss.

But his mouth made contact with yours, the warmth of his bones bringing light to all the feelings you’d been trying to fight back for so long. It was odd, having teeth pressed against your lips, and under normal circumstances you would have been disappointed. But you were too giddy and emotional and so fucking drunk, that you were willing to accept what was happening at face value.

And then he bit your lip. You hissed in shock, all the warmth and love quickly retreating back into the safety of your heart. You opened your mouth to protest, to voice a complaint that your brain hadn’t even fully developed. But all words were lost when he took the opportunity to invade your parted lips with his tongue.

You didn’t even know he _had_ a tongue, and you squealed around the slimy appendage. He must have took that as a sign that something was wrong, and quickly began pulling back. Something clicked in you at that moment, and for the first time ever you were able to react without missing a beat.

Your tongue followed his as it retreated back into his mouth. You found yourself pressed into him, the sudden momentum knocking you both off balance as you crashed to the floor. But you didn’t pause for a moment, your desire to kiss him properly overtaking you completely.

Sans grunted as he hit the floor, shocked at the eagerness with which you reciprocated. But he didn’t hesitate to catch you, hands finding their way to your hips as he kissed back in earnest. Your tongues wrestled as you straddled him, hands roaming as things turned more passionate. It didn’t matter that the two of you were drunk, it didn’t matter what would happen tomorrow. All that mattered was the miracle happening between you at the very moment.

As you parted for air, you couldn’t help but notice the way he groped at your hips, his expression helpless as he panted for that much needed oxygen. Your gazes met, and devious smiles spread across both of your faces as you caught your breath. Tomorrow would just have to wait, cuz this would be a night to remember.


	3. Day 2: Grinding

**Notes for the Chapter:**

> swap sans x reader. Grinding. I don't know why I think I can come up with dialogue. 
> 
> Also, I'm late. Big surprise there!

Your boyfriend was magnificent. Charming, friendly, filled with boundless energy. He did good deeds everywhere he went, got along with everyone. He was always busy with something, picking up odd jobs in addition to his usual responsibilities. Yet somehow he always made time for you.

You were astounded when he had asked you out. By the looks you got from his friends, they were too. At first, you had thought that it was because you were human. At the time, the possibility of interracial relationships were a shakey subject, and you certainly got your fair share of looks from your own species as well.

But the odd looks and suspicious behavior didn't subside over time. Even as monsters and humans began to mingle more, even as the number of humans around Sans increased, his friends continued to give you that strange look….

It wasn't until sans had confided his frustrations that you began to understand. He was short, energetic, optimistic. And as such, was often mistaken for or treated as a child. His friends often underestimated how well he understood situations, and humans often thought he was nothing more than a kid. 

It made sense, after that. You had seen him as an individual, someone whom you grew fond of and developed feelings for. You never once considered him as a kid. He was, after all, way older than you. Even by monster standards, he didn't wear stripes and even practically raised his brother. And yet, by agreeing to date him, they began to see you as a threat. Someone who would _ corrupt_ their sweet little skeleton.

Which you had thought to be ridiculous, honestly. He was clever, witty, and a huge flirt. He always seemed to know what to say to fluster you, what to do and where to go for dates. He even joked about it, talking about dating manuals and what level of the relationship the two of you were at.

_If there was a manual, this man had it memorized._

But, if this manual existed, it didn't mention anything of a sexual nature. Sans was a perfect gentleman. His kisses were chaste brushings of boney teeth against your skin. His hands never roamed, even when you were snuggled right up against him. 

Even now, curled against him on the couch, your body lax and welcoming in his embrace, he did nothing. Some movie was playing in the background, a choice the two of you had agreed on for date night, but you weren't paying attention. 

Instead, you found yourself studying him for the millionth time. The way magic warmed his osseous composition, his bones warm and inviting. The way his bones connected, fused together with a malleable substance at the joints. His structure was nothing like a humans, his bones were rounded, stockier, and his skull was much rounder.

You loved looking at his skull. He was so round, so cute. Your eyes were always drawn directly to that smile. It was so handsome, so charming. His eyes were easy to get lost in. Deep pools of abyss, with bright, sharp pin pricks that focused on whatever had his attention. They would change shapes too, stars for excitement, heart for affection.

Times like this reminded you just how inhuman he really was. You didn't even know if he had the...equipment..for more intimate gestures. Or any sort of interest in trying. But still, a part of you wished he'd at least consider fooling around.

**"is everything alright, my love?"**

Of course Sans noticed you spacing, you hadn't made any sort of commentary on the movie at all. He turned his attention towards you, his eyes soft, and smile warm. Upon noticing that you had been focused on him, he leaned forward and nuzzled his nasal ridge against your nose.

"Mmmm, just thinkin", you murmured. You nuzzled back, eager for any form of affection he could give you. It felt selfish to want more, when he was so sweet and full of love. He pulled back, a playful smirk on his face as he studied you.

**"with the way you've been staring, i'm feeling inclined to ask what you're thinkin’ about."**

You wanted to flirt, start up some teasing banter that never failed to add color to his boney cheeks. But...maybe if you tried discussing a more intimate relationship then he might start considering it… You bit your lip as you weighed your options, but apparently you took too long to answer. Sans tucked his finger under your chin, angling your face up so he could make eye contact. 

**"is something wrong, my dear?"**

His smile faltered, and you felt bad for making him worry. You leaned forward and nuzzled him again eager to wipe away his concerns.

"No! No, I was just...thinking about your dating manual"

Well, you guess this conversation was happening after all. You hadn't meant to say it, but it was impossible for you to lie when your boyfriend got worried. His eyes brightened at the mention of his manual, and a deep chuckle rumbled from his chest.

**"is that all? what is it you're wanting to know?"**

"Well…", you hesitated, unsure of how to proceed. You didn't want him to think you were put off, or expecting more than he could give. "...I was wondering…", an idea came to your mind, and you climbed into his lap as you finished your statement. "...what the next stage of our relationship is supposed to be?"

Your face stayed close to his, keeping the already established level of intimacy as you mounted him. You felt excitement bubble in your chest as you watched the blue blush creep along his face.

**"th-the next...step?"**

“Mhmm.” 

Sans never stuttered. He was always so confident, so sure of everything he did. Hearing him stumble over his own words was exhilarating, and you couldn’t help the swell of pride as you heard him. You pressed your forehead against his, sticking to established forms of endearment as you waited patiently for him to catch up and provide an answer.

Your boyfriend inhaled deeply, trying to steady himself as you continued to show as much affection as possible. His body relaxed on the exhale, his hands finding resting points on your body. One rested gently on your thigh, down close to the knee, while the other rested on your waist, just above your hips. 

**“i...might have been...nervous...about moving forward”**

He may as well have been a blueberry with how much color he’d developed, and you couldn’t help the smile that crept up on your face. As tame as it was, your heart was racing at the feeling of his hands on you. You wanted to see just how far he’d be willing to go, but you didn’t want to push him out of his comfort zone either. You could feel yourself blushing anyways, and hoped you didn’t end up scaring him away.

“Maybe if you tell me about it, I can help ease some of these nerves?”

You ran your hands along his shoulders, trying to reassure him. But you couldn’t help but note the way his bones felt under the fabric, couldn’t help the way your touch lingered, the way your fingers roamed. His grip tightened on your leg, fueling the growing excitement building within you. He started nuzzling you back, his confidence slowly returning as he responded.

**"i wasn't sure if you would want to proceed with more intimate behavior...since i'm not human."**

Your grip on his shoulder tightened. Sans had thought being a monster was...bad? Under normal circumstances, you would have laughed off the ridiculous notion, but now you were on a mission. You’d erase those thoughts from his mind, let him know just how much you liked him being a monster. 

“Why would you think that~”

You didn’t wait for a response before pressing your lips against his teeth. You repeated the action again, and again, and again, not giving him a chance to respond as you peppered him with smooches. You were pleased when you felt his mouth lifting back into a smile, but it didn’t mean you were done.

You trailed away from his mouth, giving him the chance to answer when he was ready, as you continued your assault on his bones. You smooched the corner of his smile, all over his cheeks, relishing in the small chuckle he let slip, before trailing your lips down his face and towards his neck.

**“i….ah...you...i-if you keep doing tha-at, i might lose control”**

That piqued your interest. The idea of Sans losing his composure, unable to control himself was just too tempting to pass up. You deliberately smooched each individual vertebrae, your dominant hand leaving his shoulder to graze softly down his ribs as you murmured “You don’t have to control yourself around me, sans.”

As if your words were the trigger he needed, your boyfriends hands began to roam. The hand on your waist wasted no time grabbing and squeezing at your hip. The other, however, took it’s time moving up your leg, kneading and squeezing in time with your kisses. His boney hand ghosted softly over your ass before giving it a tentative squeeze. You gasped, pulling away from his neck to once again look at his face.

The two of you exchanged a look, eyes lidded, faces flushed. You couldn’t help but mirror the dopey grin spread across his face. It felt good to know he was enjoying this, that he wanted to touch you. You leaned forward to plant another kiss on his teeth, but paused as you saw his mouth starting to open. It was fascinating to watch, and you found yourself mesmerized by the way his face moved.

**“may i..try something?”**

Even now, he was asking permission. You shifted in his lap, pressing your body closer to his as you nuzzled him.

“I thought you could do anything.” It was a claim he had made many times, in other contexts, but you couldn’t help but tease him with it now.

His eyes started to glow, an eerie, beautiful blue illuminating the space around you. His grip on your ass and hip tightened, pressing you firmly down onto his pelvis. What greeted you _wasn’t bone_, and you couldn’t help but cling to his ribs as you let out a surprised moan. He must have taken that as a good sign, making use of your surprised state to slip something slimy and warm into your mouth.

You were pretty sure your brain was short circuiting as he kissed you with what you could only assume was the monster equivalent of a tongue. You sucked eagerly on the magical appendage, hormones going wild as you tried to process what your boyfriend was doing to you.

He ground against you again, groaning against your lips as he pressed you against his member. You repeated the motion immediately after, grinding yourself downward as you hummed against his tongue. Your hands slipped under his shirt as the two of you found a rhythm, feeling along his bones as your clothed sexes rubbed against each other again and again.

It was intoxicating, finally getting the opportunity to be intimate with him, and it was almost a shame that you had to escape his tongue to breathe. You gasped and mewled as you took in some much needed oxygen, taking the opportunity to peek at him again as the two of you continued dry humping on the couch.

His eyes had morphed into those little hearts you loved so much, the glow of magic only enhancing the piercing gaze he had locked onto you. His breath was ragged, tongue still hanging from his mouth, his face fully flushed with color. The glow from his tongue was almost as bright as his eyes, and you found yourself hypnotized. 

A particularly enthusiastic thrust pulled your line of sight downwards, only to see that same glow emanating from the strained bulge in his pants. And yep, your pants needed to come off. Now. You weren’t about to blindside Sans with your exposed sex, but you needed to get rid of the extra layer, to feel...whatever _that_ was...pressed up against you. 

You peppered a few kisses against his teeth and tongue as you crept off of his lap. He whimpered, a half-choked **“what”** that never fully escaped him as he fixated on your movements. You struggled with the button on your pants, fumbling as you unfastened it and ripped the zipper down. You shimmied awkwardly, trying to keep your panties on as you wiggled the denim down over your ass.

You lost your balance as they slipped down, struggling slightly to free your feet from the offensive fabric. You fell back into sans’ lap as you freed yourself, smiling awkwardly as you threw them across the room. That was...a lot less sexy than you had pictured it in your head, but sans didn’t seem to mind. Before you could adjust your position, he stood up, lifting you bridal style and carrying your towards the bedroom. 

You had the feeling you were in for a good time.


End file.
